l8 LIVING PROTOPLASM AND 



diamid sulfate will kill a rabbit in hour (Buchncr). 



Why is it then, — it will be asked that hydroxylamin and 

 diamid are such strong poisons compared with ammonia? The 

 answer can only be found in the marked difference of behaviour 

 to aldehydes (resp. Ketons). It has been demonstrated by 

 recent investigations, that salts of hydroxylamin and of diamid 

 (hydrazin) act even in high dilutions upon aldehydes while 

 ammonia acts only as free base or as carbonate and with less 

 energy. This difference is due to the greater lability of the 

 liydrogcnatoms in the former, attacking thus easier the labil 

 oxygen of aldehydes and ketons. 



N — H N— H N— H 



\ H \ OH ^ NH 2 



Ammonia. Hydroxylamin. Diamid. 



We find analogous differences of intensity of toxicological 

 actions between anilin C 6 H 5 .NH 2 and phenylhydrazin, C fi H 5 . 

 NH.NH 2 ; between pyridin C 5 H 5 N and piperidin C 5 H I0 .NH ; 

 between phenol and amidophenol, which latter is,-m accordance 

 with the behaviour to aldehydes, -also a stronger poison than 

 anilin. — 



The reaction between hydroxylamin and an aldehyde is 



expressed by the following equation : 



=0 =N— OH 



(*)-C_ H + H 2 N-OH = (-t)-C-h +H 2 0 



An aldehyde. An aldoxim. 



It is of considerable interest, that also certain derivatives 

 of hydroxylamin react easily with aldehydes and exhibit in ac- 

 cordance therewith a poisonous character; these derivatives are 

 the "amidoxims," prepared by Tiemann by the action of con- 

 centrated hydroxylamin upon nitriles at higher temperatures : 



(*)-C=N + H a N-OH = (*)-C~S-0 H 



A nitril. An amidoxim. 



r -NH 2 =0 -N=CH-(>) n 



U)-C = N _oh + 0')-C_h = (*) — C = N-OH +H 2 0 ) 



An aldehyde. 



i) The product thus formed can undergo an atomic migration; Tiemann, 

 Ber. 22, p. 3124. 



